Affiliation:
1. Department of Applied Chemistry Graduate School of Engineering Osaka University Suita Osaka 565-0871 Japan
2. Center for Future Innovation Graduate School of Engineering Osaka University Suita Osaka 565-0871 Japan
3. Innovative Catalysis Science Division Institute for Open and Transitionary Research Initiatives (ICS-OTRI) Osaka University Suita Osaka 565-0871 Japan
Abstract
AbstractFunctionalized triptycene derivatives have attracted significant research interest because of their potential applications in many research fields. Although the conventional Diels‐Alder reaction of anthracenes with benzynes has been a versatile synthetic tool for functionalized triptycenes, it is hardly possible to control the product regioselectivity. In this report, we demonstrate the selective synthesis of 1,8,13‐trisubstituted triptycenes by Pd‐catalyzed α‐bromination. As for the directing group, SMe group was the most effective to facilitate the halogenation of the proximal three benzene rings. The obtained product was further derivatized through allylation and Rh‐catalyzed hydroboration reactions.